Process of preparing the nitriles of alpha-naphthyl substituted lower fatty acids



Patented Jan. 2, 1940 PROCESS OF PREPARING THE HITBILES OF I ALPHA-NAPHTHYL SUBSTITUTED LOWER FATTY ACIDS John Weijlard and William H. Engels, Bahway, N. J., assignors to Merck & Co. Inc.', Railway, N. 1., a corporation of New Jersey No Drawing.

7 Claims.

This invention relates to a process of preparing the nitrlles of alpha-naphthyl substituted lower fatty acids substantially free from the beta isomer and has as its object the provision of an easy '5 method of preparing'such nitriles.

It is known that alpha-naphthyl acetonitrile may be prepared by brominating alpha methyl naphthalene, and reacting the bromomethyl naphthalene with potassium cyanide. This proc- 10 ess is objectionable in that alpha methyl naphthalene is not readily obtainable. In addition, during bromination, a large amount of bromine goes into the ring, forming bromination products which are difficult to separate from the desired product. I

We have discovered that the nitriles of alphanaphthyl substituted lower fatty acids may be easily prepared with a good yield by condensing naphthaieneand-a halogenated nitrile of a lower fatty acid in the presence of anhydrous ferric chloride. Contrary to expectations the reaction goes quite smoothly. The reaction may be expressed by the following equation:

omen

Naphthalene chloracetonitrile slpha-naphthyl acetonitrile The following example illustrates one method of carrying out our invention, but it is to be uns derstood that this example is by .way of illustration and not 01' limitation.- 35 Example gm. of chloracetonitrile are mixed with 54 perature of l65 to 185 c., but best results are.

obtained at 170 to 175 c. The thick reaction a mixture is then poured onto 100 gms. oi ice; 100

cc. of concentrated hydrochloric acid are added,

and the mixture is stirred. The aqueous solution is decanted ofland, the moist semi-solid is agitated with .500 cc. of ether until disintegration 50 takes place. The mass is filtered, the resinous ether filtrate washed several times with dilute hydrochlorlcacidtoremoveiron. Theether momm 's-memorandum- Application August 11, 1937, Serial No. 158,539

tion to. precipitate any remaining'traces of iron.

Charcoal is added and the solution filtered. After evaporation of the ether, alpha-naphthyl acetonibe substituted by chlorpropionoiiitrile, chlorbu- 10 tyronitrile, etc.

The 'alpha-naphthyl acetonitrile obtained as' in the aboveexample may be used as such, or in the preparation of other compounds. For ex- .ample, it may be hydrolyzed in the known man- 15 ner to alpha-naphthyl acetic acid, which has v'aluable plant growth properties.

, Modifications may be made in carrying out our invention without departing from the spirit and scope thereof, and we are to be limited only by 20 the appended claims. a We claim;

1. The process comprising condensing naphthalene and a halogenated nitrile of r. lower fatty acid in the presence of anhydrous ferric chloride 25 at a temperature of about 165 to 185 C.

, 2. The process comprisingcondensing naphthalene and a halogenated acetonitrile in the presence of anhydrous ferric chloride at a'temperature of about ,165 to 185 C. v

3. The process comprising condensing naphthalene and chloracetonitrile in the presence of 4. The process comprising condensing naphthalene and bromacetonitrlle in the presence of anhydrous ferric chloride at a temperature-oi about 165-185" C.

' 5. The process comprising condensing naphthalene and bromacetonitrlle in the presence of anhydrous ferric chloride at a temperature of about 170 to 175 C.

6. The process comprising condensing naphthalene. and a halogenated butyronitrile in the presence of anhydrous ierric chloride 5st a tem-' perature oi about l-185 C.

'1. The process comprising condensing naphthalene and chlorbutyronitrile in the presence of anhydrous ferric chloride at a temperature of v about to C. 50 residue on the filter washed with ether. and the.

JOHN mm. wit-muss. 

